Tracking the Pathways of Peptoid Fragmentation
Poster Number
16B
Format
Poster Presentation
Faculty Mentor Name
Jianhua Ren
Faculty Mentor Department
Chemistry
Graduate Student Mentor Name
Yadwinder Singh Mann
Graduate Student Mentor Department
Pharm. & Chem. Sciences
Abstract/Artist Statement
In the present investigation, the fragmentation pattern of two isomeric peptoids having neutral residues was compared using mass spectrometry. Being able to understand how peptoids fragment will help to provide more insight in establishing de novo sequences of peptoid libraries. Peptoids resembles peptide in their general structure but are different than the latter because the side chains are attached to a nitrogen instead of an ɑ-carbon. Applications of peptoids in therapeutics, catalysts, molecular machine and possible information storage house in future, etc make them a wonderful synthetic polymer.
For our study, two isomeric peptoid having alternating N-(2-methyloxyethyl)glycine (Nme)and N-(2-phenylethyl)glycine (Npe) with six residues were synthesized using Solid-Phase Peptide Synthesis (SPPS) method. This method allows for the synthesis of peptoids chains sequentially on a resin. The resin is activated for peptoid synthesis by deprotecting the Fmoc group with 20% Piperidine in dimethylformamide (DMF).Peptoid synthesis involves 2 steps: bromoacetylation and displacement. In bromoacetylation, a mixture of diisopropylcarbodiimide (DIC) and bromoacetic acid is used in DMF. In the displacement step, the bromine in the peptoid is displaced with the amine of choice in DMF solution. These bromoacetylation and displacement reactions were repeated until a desired sequence of peptoid was synthesized. After synthesis, the final step involves cleavage and purification. The fragmentation patterns of the peptoids were analyzed using Mass Spectrometry. The SPPS method was shown to be an efficient protocol for peptoid synthesis and resulted in products with high yield. The peptoids were found to follow the same type of fragmentation pattern regardless of the side chain.
After gaining insight on peptoid fragmentation, this knowledge will be used for further examination on how acidic and basic side chains will affect peptoid fragmentation patterns.
Location
DeRosa University Center Ballroom
Start Date
27-4-2018 10:00 AM
End Date
27-4-2018 12:00 PM
Tracking the Pathways of Peptoid Fragmentation
DeRosa University Center Ballroom
In the present investigation, the fragmentation pattern of two isomeric peptoids having neutral residues was compared using mass spectrometry. Being able to understand how peptoids fragment will help to provide more insight in establishing de novo sequences of peptoid libraries. Peptoids resembles peptide in their general structure but are different than the latter because the side chains are attached to a nitrogen instead of an ɑ-carbon. Applications of peptoids in therapeutics, catalysts, molecular machine and possible information storage house in future, etc make them a wonderful synthetic polymer.
For our study, two isomeric peptoid having alternating N-(2-methyloxyethyl)glycine (Nme)and N-(2-phenylethyl)glycine (Npe) with six residues were synthesized using Solid-Phase Peptide Synthesis (SPPS) method. This method allows for the synthesis of peptoids chains sequentially on a resin. The resin is activated for peptoid synthesis by deprotecting the Fmoc group with 20% Piperidine in dimethylformamide (DMF).Peptoid synthesis involves 2 steps: bromoacetylation and displacement. In bromoacetylation, a mixture of diisopropylcarbodiimide (DIC) and bromoacetic acid is used in DMF. In the displacement step, the bromine in the peptoid is displaced with the amine of choice in DMF solution. These bromoacetylation and displacement reactions were repeated until a desired sequence of peptoid was synthesized. After synthesis, the final step involves cleavage and purification. The fragmentation patterns of the peptoids were analyzed using Mass Spectrometry. The SPPS method was shown to be an efficient protocol for peptoid synthesis and resulted in products with high yield. The peptoids were found to follow the same type of fragmentation pattern regardless of the side chain.
After gaining insight on peptoid fragmentation, this knowledge will be used for further examination on how acidic and basic side chains will affect peptoid fragmentation patterns.